EP 0164290 A1 19851211 - Process for the dealkylation of alcaloids and intermediates.
Title (en)
Process for the dealkylation of alcaloids and intermediates.
Title (de)
Verfahren zur Dealkylierung von Alkaloiden und Zwischenprodukte.
Title (fr)
Procédé de déalkylation d'alcaloides et intermédiaires.
Publication
Application
Priority
FR 8408273 A 19840525
Abstract (en)
1. A process for the dealkylation of 14-hydroxymorphinan alkaloids, characterized in that it consists in : 1) reacting the 14-hydroxy derivative of the formula : see diagramm : EP0164290,P5,F6 in which R' is CH3 or COCH3 , with excess ethyl chloroformate, in the presence of potassium carbonate and in a solvent, 2) subjecting the resulting carbamate of the formula : see diagramm : EP0164290,P5,F2 in which R' is CH3 or COCH3 , to hydrolysis in a strong acid medium to give the corresponding dealkylated derivative of the formula : see diagramm : EP0164290,P5,F3 in which R is CH3 or hydrogen.
Abstract (fr)
Procédé de déalkylation des alcaloïdes 14-hydroxymorphinanes. Ce procédé consiste à faire réagir un dérivé 14-hydroxylmorphinane avec du chloroformiate d'éthyle en excès en présence de carbonate de potassium au sein d'un solvant, à soumettre ensuite le carbamate obtenu à une hydrolyse en milieu acide fort. Application: déméthylation de la thébaïne.
IPC 1-7
IPC 8 full level
C07D 489/00 (2006.01); C07D 489/08 (2006.01)
CPC (source: EP)
C07D 489/08 (2013.01); Y02P 20/55 (2015.11)
Citation (search report)
- [A] FR 2515184 A1 19830429 - UNIV FLORIDA STATE [US]
- [AD] US 4141807 A 19790227 - VIA FRANCIS A
- [A] US 4390699 A 19830628 - BROSSI ARNOLD, et al
- [A] FR 2395269 A1 19790119 - WARNER LAMBERT CO [US]
- [AD] JOURNAL OF MEDICINAL CHEMISTRY, vol. 15, no. 2, février 1972, pages 208-210, Columbus, Ohio, US; M.M. ABDEL-MONEM et al.: "N-demethylation of morphine and structurally related compounds with chloroformate esters"
Designated contracting state (EPC)
AT BE CH DE FR GB IT LI LU NL SE
DOCDB simple family (publication)
EP 0164290 A1 19851211; EP 0164290 B1 19890906; AT E46163 T1 19890915; AU 4284385 A 19851128; AU 577379 B2 19880922; CA 1244825 A 19881115; DE 3572819 D1 19891012; DK 160048 B 19910121; DK 160048 C 19910617; DK 227685 A 19851126; DK 227685 D0 19850522; ES 543338 A0 19860101; ES 8603893 A1 19860101; FR 2564838 A1 19851129; FR 2564838 B1 19861107; JP S60258183 A 19851220; NO 164981 B 19900827; NO 164981 C 19901205; NO 852091 L 19851126; NZ 212193 A 19881028; PT 80519 A 19850601; PT 80519 B 19880122
DOCDB simple family (application)
EP 85400996 A 19850521; AT 85400996 T 19850521; AU 4284385 A 19850524; CA 482102 A 19850522; DE 3572819 T 19850521; DK 227685 A 19850522; ES 543338 A 19850521; FR 8408273 A 19840525; JP 11301685 A 19850524; NO 852091 A 19850524; NZ 21219385 A 19850524; PT 8051985 A 19850523